NZ501835A - Process for the preparation of a substituted perhydroisoindole - Google Patents
Process for the preparation of a substituted perhydroisoindoleInfo
- Publication number
- NZ501835A NZ501835A NZ501835A NZ50183598A NZ501835A NZ 501835 A NZ501835 A NZ 501835A NZ 501835 A NZ501835 A NZ 501835A NZ 50183598 A NZ50183598 A NZ 50183598A NZ 501835 A NZ501835 A NZ 501835A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- compound
- produce
- medium
- salt
- Prior art date
Links
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical class C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000008064 anhydrides Chemical class 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 239000010948 rhodium Substances 0.000 abstract 2
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- BFMKBYZEJOQYIM-UCGGBYDDSA-N tert-butyl (2s,4s)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound C([C@@H]1C[C@@H](CN1C(=O)OC(C)(C)C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BFMKBYZEJOQYIM-UCGGBYDDSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Abstract
The industrial preparation of a substituted perhydroisoindole of formula (I) or a pharmaceutically acceptable salt thereof comprises: a) reacting dimethyl succinate with benzaldehyde in a methanolic medium to produce the diacid of formula (II); b) the diacid (II) is heated in an aprotic medium in the presence of acetic anhydride to produce the anhydride of formula (III); c) the anhydride (III) is reacted with perhydroisoindole of formula (IV) in an aprotic solvent to produce the compound of formula (V); d) compound (V) is subjected to catalytic hydrogenation using as asymmetric hydrogenation catalyst the complex rhodium/(2S, 4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphino-methylpyrrolidine or Rh/(S,S) BPPM in methanolic or methylene chloride medium followed by conversion to a salt in the presence of an amine A to produce a compound of formula (VI); e) compound (VI) in a basic medium in the presence of a mineral salt yields an addition salt of the compound of formula (I) which is converted optionally into the corresponding acid or f) compound (VI) in an acidic medium yields the compound of formula (I) which is converted optionally into a pharmaceutically acceptable addition salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9708431A FR2765578B1 (en) | 1997-07-03 | 1997-07-03 | PROCESS FOR THE PREPARATION OF A SUBSTITUTED PERHYDROISOINDOLE |
| PCT/FR1998/001405 WO1999001430A1 (en) | 1997-07-03 | 1998-07-01 | Method for preparing a substituted perhydroisoindole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ501835A true NZ501835A (en) | 2000-11-24 |
Family
ID=9508815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ501835A NZ501835A (en) | 1997-07-03 | 1998-07-01 | Process for the preparation of a substituted perhydroisoindole |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6133454A (en) |
| EP (1) | EP0994854B1 (en) |
| JP (1) | JP4056093B2 (en) |
| KR (1) | KR100421073B1 (en) |
| CN (1) | CN1108291C (en) |
| AT (1) | ATE224368T1 (en) |
| AU (1) | AU734398B2 (en) |
| BR (1) | BR9810657A (en) |
| CA (1) | CA2295992C (en) |
| DE (1) | DE69808092T2 (en) |
| DK (1) | DK0994854T3 (en) |
| EA (1) | EA002151B1 (en) |
| ES (1) | ES2184304T3 (en) |
| FR (1) | FR2765578B1 (en) |
| HK (1) | HK1028610A1 (en) |
| HU (1) | HUP0002778A3 (en) |
| NO (1) | NO313095B1 (en) |
| NZ (1) | NZ501835A (en) |
| PL (1) | PL190861B1 (en) |
| PT (1) | PT994854E (en) |
| WO (1) | WO1999001430A1 (en) |
| ZA (1) | ZA985882B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2793411B1 (en) * | 1999-05-11 | 2001-06-29 | Synthelabo | USE OF SUCCINIC ACID DERIVATIVES FOR OBTAINING A MEDICAMENT FOR THE TREATMENT OF INFLAMMATION |
| FR2834892B1 (en) * | 2002-01-23 | 2004-02-27 | Servier Lab | ORODISPERSIBLE PHARMACEUTICAL COMPOSITION OF MITIGLINIDE |
| US6684422B2 (en) * | 2002-02-27 | 2004-02-03 | Ginger Magnolia | Toy retention blanket and system |
| WO2004002474A1 (en) * | 2002-06-28 | 2004-01-08 | Kissei Pharmaceutical Co., Ltd. | Drug composition for prevention or inhibition of advance of diabetic complication |
| KR100709528B1 (en) * | 2002-06-28 | 2007-04-20 | 깃세이 야쿠힌 고교 가부시키가이샤 | Drug composition for blood sugar control |
| CN1304409C (en) * | 2002-08-23 | 2007-03-14 | 万有制药株式会社 | Process for producing indolopyrrolocarbazole derivative |
| FR2860231B1 (en) * | 2003-09-25 | 2005-11-18 | Servier Lab | NOVEL PROCESS FOR PREPARING CIS-OCTAHYDRO-ISOINDOLE |
| US7230022B2 (en) * | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| CN1634885B (en) * | 2004-11-09 | 2011-05-04 | 北京乐力健生物科技有限公司 | Novel mitiglinide crystalline form and its preparing process |
| CN1324010C (en) * | 2005-01-12 | 2007-07-04 | 江苏省药物研究所 | Preparation of miglitol |
| JP4918257B2 (en) * | 2005-12-27 | 2012-04-18 | キッセイ薬品工業株式会社 | Asymmetric reduction method |
| WO2009047797A2 (en) * | 2007-10-08 | 2009-04-16 | Ind-Swift Laboratories Limited | Process for the preparation of perhydroisoindole derivative |
| CN102382033B (en) * | 2010-08-31 | 2013-04-03 | 凯瑞斯德生化(苏州)有限公司 | Preparation methods for optical activity mitiglinide ester and mitiglinide salt |
| CA2838749A1 (en) | 2011-06-10 | 2012-12-13 | Bluebird Bio, Inc. | Gene therapy vectors for adrenoleukodystrophy and adrenomyeloneuropathy |
| KR101327866B1 (en) * | 2011-10-27 | 2013-11-11 | 주식회사 메디켐코리아 | Improved process for preparing Mitiglinide calcium salt |
| WO2013189829A1 (en) | 2012-06-22 | 2013-12-27 | Laboratorios Lesvi, S. L. | Process for obtaining (s)-2-benzyl-4-((3ar,7as)-hexahydro-1 h-isoindol- 2(3h)-yl)-4-oxobutanoic acid and salts thereof |
| CN103450069B (en) * | 2013-06-24 | 2015-04-15 | 山西大同大学 | Preparation method of mitiglinide calcium |
| CN103709092B (en) * | 2013-11-04 | 2016-07-06 | 河北科技大学 | The preparation method of Mitiglinide Calcium |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU654331B2 (en) * | 1991-03-30 | 1994-11-03 | Kissei Pharmaceutical Co. Ltd. | Succinic acid compounds |
-
1997
- 1997-07-03 FR FR9708431A patent/FR2765578B1/en not_active Expired - Fee Related
-
1998
- 1998-07-01 NZ NZ501835A patent/NZ501835A/en unknown
- 1998-07-01 CN CN98806779A patent/CN1108291C/en not_active Expired - Fee Related
- 1998-07-01 JP JP50653499A patent/JP4056093B2/en not_active Expired - Fee Related
- 1998-07-01 AT AT98935072T patent/ATE224368T1/en not_active IP Right Cessation
- 1998-07-01 CA CA002295992A patent/CA2295992C/en not_active Expired - Fee Related
- 1998-07-01 ES ES98935072T patent/ES2184304T3/en not_active Expired - Lifetime
- 1998-07-01 WO PCT/FR1998/001405 patent/WO1999001430A1/en active IP Right Grant
- 1998-07-01 EA EA200000094A patent/EA002151B1/en not_active IP Right Cessation
- 1998-07-01 EP EP98935072A patent/EP0994854B1/en not_active Expired - Lifetime
- 1998-07-01 US US09/446,848 patent/US6133454A/en not_active Expired - Fee Related
- 1998-07-01 DK DK98935072T patent/DK0994854T3/en active
- 1998-07-01 BR BR9810657-0A patent/BR9810657A/en not_active Application Discontinuation
- 1998-07-01 PT PT98935072T patent/PT994854E/en unknown
- 1998-07-01 DE DE69808092T patent/DE69808092T2/en not_active Expired - Lifetime
- 1998-07-01 PL PL337728A patent/PL190861B1/en not_active IP Right Cessation
- 1998-07-01 HU HU0002778A patent/HUP0002778A3/en unknown
- 1998-07-01 AU AU84450/98A patent/AU734398B2/en not_active Ceased
- 1998-07-02 KR KR10-1998-0026520A patent/KR100421073B1/en not_active IP Right Cessation
- 1998-07-03 ZA ZA985882A patent/ZA985882B/en unknown
-
1999
- 1999-12-30 NO NO19996577A patent/NO313095B1/en not_active IP Right Cessation
-
2000
- 2000-12-15 HK HK00108117A patent/HK1028610A1/en not_active IP Right Cessation
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